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Literary Bad Boys

In preparation for Emily Bronte’s birthday, we’re thinking of Wuthering Heights’ quintessential romantic anti-hero: Heathcliff.

Laurence Olivier as Heathcliff. Image ID 156736

In his honor, we asked our book experts here at The New York Public Library: Who’s your favorite literary bad boy and why? The more tortured, the better.

Literary Fiction


I am currently crushing on the mysterious, unattainable Jake in Stephanie Danler’s Sweetbitter. Jake—tall, golden-eyed, effortless, moody, damaged, elusive, evasive, partially hidden tattoos. Here’s to all the bartenders in all the restaurants where I waited tables who were way out of my league. Cheers, boys! —Lynn Lobash, Readers Services





special topics

In Special Topics in Calamity Physics, author Marisha Pessl writes a prep school murder mystery. Pessl's character, Blue Van Meer, loves to cite literature and pop culture. She learns Spanish so she can communicate with the handsome Peruvian gardener her father hired. 

“...I couldn’t let go of the thought that it had, in fact, been he, restless and moody Heathcliff. Day after day, he floated through all the Wal-Marts in America, searching for me in a million lonely aisles.” 

While Blue and the other characters in STiCP are not anti-heroes per se, rebels abound in the text: “I was next to Amadeus and some sad kid who was the spitting image of Sal Mineo (see Rebel Without a Cause).” —Jenny Baum, Jefferson Market

Young Adult & Children


What adolescent girl didn’t fall in love with all of the guys from S.E. Hinton’s The Outsiders? And even though the movie was fairly mediocre, it was full of 80’s heartthrobs, which totally redeemed it. Stay gold, Ponyboy. —Rebecca Donsky, 67th Street






city bones

I can’t think of anyone more tortured and twisted than Jace Wayland of Cassandra Clare’s The Mortal Instruments series. A skilled demon hunter who can protect you, a tragic family history that just gets progressively worse, and brooding for days. —Lauren Bradley, 53rd Street





Photo from Flickr.

I have to go with Severus Snape, the very unpleasant anti-hero of the Harry Potter series. Tortured already by a life-long love that was never to be realized, he was bullied relentlessly by the person who stole his love away. The anger that built from his tormented childhood urged him to join the dark side, until the Potters were murdered by the same dark wizard that Snape worshiped. Readers only find out Snape’s critical role in the series at the very end, and by that point, we understand how deeply he loved Lily Potter, how important that love was for, and how good a guy he really was. You hate to love him, but you can’t help it. —Katrina Ortega, Hamilton Grange


Photo from Fandom Transparents.

I completely agree with Katrina about Snape, and I’d like to add Draco Malfoy to this list. He’s the bad boy who had no choice but to be bad. His father was evil. He literally had Moldy Voldy living in his house. He didn’t realize he had the choice not to be bad until it was too late. Draco is the character that most intrigued me in the Harry Potter series because I always wondered what he could have been if he had not been bogged down by his father’s philosophy. He never had a chance until it was too late. —Grace Loiacono, St. George



holden caulfield

Holden Caulfield, the narrator and protagonist of the J.D. Salinger’s The Catcher in the Rye. Kicked out of prep school and in New York by himself, Holden is constantly brooding and on alert for phonies. He’s the quintessential misanthrope, yet he craves the connections he avoids. Mixed signals… typical “baby boy” behavior. *rolls eyes* —Jhenelle Robinson, Morrisania





Graphic Novels


Cowboy. Criminal. Vampire. Skinner Sweet, the eponymous antihero of Scott Snyder’s graphic novel series American Vampire, is an antihero vampire for a new generation.  —Emily Merlino, Yorkville







My immediate thought is Wolverine from the X-Men comic franchise. He is tortured (literally), hard to read, has crazy wild hair, and rides a motorcycle. (Plus, he and Jean Grey from Dark Phoenix are star crossed lovers!) —Amie Wright, MyLibraryNYC








I’ve always had a thing for the boys with red eyes. First it was Dark Heart, from Care Bears II (100% dating myself here), but then I found Steerpike. Mervyn Peake’s Gormenghast anti-hero is intelligent, devious, twisted, and absolutely the kind of bad boy you know is all wrong but can’t help falling for anyway. —Kay Menick, Schomburg Center






Ferdinand Bardamu from Celine’s Journey to the End of the Night is a relentless, exultantly cynical and pessimistic nihilist and misanthrope whose character is only fully realized when surrounded by war, illness, and death. The ultimate “bad boy.” —Lauren Restivo, 115th Street







Hands down, Humbert Humbert, of Lolita fame. Nabokov’s most scandalous and salacious narrator, H.H. is movie-star handsome, professorial, and hopelessly hilarious--for a liar, kidnapper, murderer, and pedophile. He plays delicious word games with his readers, and seeds his narrative with clues, cues, and letter-Q’s, all distractions from the pain and suffering his desires inflict upon poor Dolores Haze. I can’t recommend Alfred Appel’s Annotated Lolita enough! —Nancy Aravacz, Jefferson Market





My BBBF (best bad boy forever) is Macheath—a.k.a., Mack the Knife—in Bertolt Brecht’s The Threepenny Opera. Charming and cold-blooded, a genuine sociopath, he’s completely indestructible. And you have to listen to Kurt Weill’s songs from the famous Theatre de Lys production to get the full effect. —David Nochimson, Pelham Parkway-Van Nest






Dean Moriarty from Jack Kerouac’s On The Road. Dean’s clearly a very persuasive character, and his judgment is not always the best. His reckless behavior and suggestions don’t always bode well for some of the book’s more gentle characters like Sal and Ed. —Joseph Pascullo, Grand Central





Jack London’s protagonist, Martin Eden. Not sure if he counts as exactly a rebel, per se. But he’s certainly tortured and brooding. That guy always made me swoon. How can any librarian not love the way he pored over books in the library till the wee hours, forcing himself to read and write past his comfort level in order to converse with Ruth Morse?! Be still, my heart! —Anne Barreca, Battery Park City

Science Fiction & Fantasy


Jacqueline Carey’s follow up series to the first three Kushiel’s Legacy books comes Prince Imriel’s saga in Kushiel’s Scion. Son of a traitor, but scion to a great house, Imriel faces the ridicule of court. It doesn’t matter to him though, he’s faced worse. However, things start to go awry when he falls for the crown princess Sidonie. Though she returns his love, it not one that is accepted and he marries another in hopes of doing what’s best for Sidonie. But is it really for the best? —Chantalle Uzan, Francis Martin






My immediate thought was to Lestat, the narrator in Anne Rice’s long series beginning with Interview with the Vampire and The Vampire Lestat. He revels in being Bad with a capital B.  Drinking in blood and life in equal measures, he leaves a wake of destruction in his path. However, as he develops relationships with people and vampires over the centuries, he winds up accidentally doing much more good than bad. —Erin Arlene Horanzy, Francis Martin


Mystery, Horror, Romance


One of my favorite bad boys is Pietro “Bearclaw” Brnwna, from Josh Bazzell’s Beat the ReaperPietro is the ultimate bad boy with a heart of gold. He’s a former mob hitman turned doctor extraordinaire hellbent of avenging the deaths of his beloved grandparents.  —Annie Lin, Mulberry Street






Perhaps not a romantic choice, but I am a huge fan of Hannibal Lecter. Yes, yes, he is a cannibal and villain, but he is also brilliant and engaging. You can find him in Red Dragon, The Silence of the Lambs, Hannibal, and Hannibal Rising. As the series progresses, you are able to fully delve into his complex, elegant, and sinister mind and see Lecter evolve from antagonist to protagonist. —Alexandria Abenshon, Yorkville






dark tower

My first thought is definitely Eddie Dean from Stephen King’s Dark Tower series. Hes an ex-heroin addict from NYC with a heart of gold and a great shooting hand. Too bad he falls for another gunslinger throughout the course of the series... —Alessandra Affinito, Chatham Square







I have a thing for rakes, rogues, and romance. One of my favorite romance writers is Jo Beverley and I wrote a whole blog post on my love for her “Company of Rogues” series and all the companion novels that go along with it. The lead rogue is Nicholas Delaney and he’s a rogue spy, seducing women for information when he’s not rescuing damsels in distress in An Arranged Marriage. The second book, An Unwilling Bride, has haughty rogue Marquess of Arden forced to marry an independent schoolteacher to save his inheritance. But my absolute favorite is The Devil’s Heiress, which finds brooding rogue Major George Hawkinville returning from Waterloo only to discover that his estate has been inherited by the quiet and plain Clarissa, fiancé of the unscrupulous Lord Deverill. —Anne Rouyer, Mulberry Street



Have trouble reading standard print? Many of these titles are available in formats for patrons with print disabilities.

Staff picks are chosen by NYPL staff members and are not intended to be comprehensive lists. We'd love to hear your ideas too, so leave a comment and tell us what you’d recommend. And check out our Staff Picks browse tool for more recommendations!


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My Mae West's plays are "Courting Mae West" and "Diamond Lil: Queen of the Bowery" -- and I have been organizing Mae West events since 2003. Here is my next NYC library event on August 17, 2016, celebrating Mae West on her birthday in the same room where she faced a Jefferson Market judge who sent her to jail ----: Mae's novel, set in Harlem, "Babe Gordon" --

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